Jump to content

Neber rearrangement

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by KLBot2 (talk | contribs) at 01:17, 23 April 2013 (Bot: Migrating 1 interwiki links, now provided by Wikidata on d:Q904114). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

The Neber rearrangement is an organic reaction in which an oxime is converted into an alpha-aminoketone in a rearrangement reaction.[1][2]

Neber rearrangement

The oxime is first converted to a ketoxime tosylate by reaction with tosyl chloride. Added base forms a carbanion which displaces the tosylate group in a nucleophilic displacement to an azirine and added water subsequently hydrolyses it to the aminoketone.

The Beckmann rearrangement is a side reaction.

References

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
  2. ^ P. W. Neber and A. v. Friedolsheim (1926). "Über eine neue Art der Umlagerung von Oximen". Justus Liebig's Annalen der Chemie. 449 (1): 109–134. doi:10.1002/jlac.19264490108.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Neber_rearrangement&oldid=551724504"